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We did everything for it to go just right... but it didn't.

My girlfriend and I are both non-op transsexuals; (i.e., she's MtF, I'm FtM, and we haven't had "the surgery" and don't intend to.) On a visit with her a little while ago, she and I were sitting in her car and talking about our feelings regarding sex. When our relationship started over a year ago she asked me to wait, which I was fine with, but didn't know she had been open to what we considered "in between" kind of stuff like oral (she doesn't want to go "all the way" because she was raped a little while before I met her and she feels like penetrating me is putting me in her position--it isn't, but I'm not going to pressure her), and while we had been discussing it we realized we were both in the mood and I asked her if she wanted to find some place more private and explore, and she said "only if you want to." I did.
Before we got started, I asked her if she still wanted to continue and if she had any other boundaries she wanted to set in place, and she said no. I reminded her that if she wanted me to stop at any time she could say so and I would stop everything.

Heather Corinna replies:

Hedo's question continued: While I was working with her and experimenting with what she liked I got a lot of positive feedback and encouragement. It was very clear that she was enjoying what I was doing, which felt amazing for me, too. But after we finished and cleaned up she got withdrawn and awkward, and we didn't talk much on the way back to her friend's apartment. What I could get out of her was that she felt guilty for being the only one who got off (part of why she didn't reciprocate was her fear of getting me pregnant, and having trouble working with how fickle my body is, so it wasn't an issue for me), and, just before we got back to the apartment, she confessed that she might not have been as ready as she felt. She kept apologizing until we each went to sleep, no matter how much I tried to convince her that it wasn't her fault.

Later that morning when we were able to talk it over more I kept reminding her that it's hard to make good decisions in the heat of the moment and that it's okay to feel regret, that I didn't expect perfection, and that even under the best circumstances sex is complicated and I'm willing to wait again. But she still feels bad.

Is there anything more I can say and do to help her feel better now, or the next time we have a sexual experience, or should we put it away for a while and let her sort through some of her feelings, first? And is it wrong/unfair to her for me to think of how she climaxed and be as turned on by it as I am? Because when I do I can't help but think I'm not respecting her feelings.

I don't think either of you made any major missteps, or said, did or felt anything that wasn't okay or was in any way intentionally hurtful to one another or yourselves. I'm seeing excellent sexual communication (better than most people tend to have), phenomenal understanding, empathy and acceptance of differences in your sexual wants and readiness, clear and enthusiastic consent (and all the room in the world for easy nonconsent), and a whole lot of sensitivity and mutual care. I don't think one can go about this any better than you both did. If there was an Oscar for sexual communication and negotiation, you two'd get it this year, no contest.

There seem to be two central issues here: her feeling like she was ready in advance of sex and then, afterwards, feeling like she may not have been and her feeling guilty or unhappy that she had an orgasm while you did not. There is also the issue of you feeling guilty because she feels conflicted about her decision to have sex, but you found her experiencing what she did with you sexy. Obviously, too, you want to figure out how to move forward from here. Most of what I have to say is going to be about pieces one or both of you may or may not have that you can talk about moving forward. You may have even talked about some of them already.

Let's start with pleasure and orgasm. Orgasm isn't necessarily an indication of pleasure or satisfaction, even though it often is. Orgasm also isn't necessarily an indication that in a scenario where one person reaches orgasm and the other does not, the person who reached orgasm was more satisfied or had a more pleasurable experience than the other, even though that can and does certainly happen. What orgasm is, for the most part, is a whole-body reaction to nervous system stimulation, usually -- but not always -- expressly sexual stimulation, and usually -- but not always -- because we are having sexual feelings in our hearts and minds. The "not always" in both cases is important. For example, some people orgasm when they are sexually assaulted, some people do in their sleep, some people do via sensory stimulus they strongly feel is not sexual for them at all. As well, some people have good sexual experiences, even amazing ones, where they experienced pleasure and felt satisfied but did not reach orgasm, either by choice or because that's just not what happened. You may need to remind your girlfriend of that, especially if her experience is different, where she may not feel satisfied without orgasm, or have yet had an experience where she felt satisfied without it to understand that.

It's fairly common for people to expect and want both people to reach orgasm in a sexual experience. However, I'd say that's not as typical as a lot of folks imagine, and it is particularly uncommon when anyone is new to sex, or when any kind of sex is new in a given relationship. Often, it takes time for people to get comfortable enough to let go physically and emotionally so they can reach orgasm, and it can also take time for people to learn each others bodies (including our own) well enough for that to happen frequently. It's safe to say that for people on the whole, all people involved in sex reaching orgasm every single time is the great exception, rather than the rule. It's also typical for people to either not recognize, overlook or undervalue the fact that when we're really into someone, our experience of pleasure isn't usually just self-centered, but about what's happening with our partner. In other words, you very clearly did enjoy yourself, and got a lot of pleasure and satisfaction from the pleasure she was experiencing. This is something you might want to talk about with her if you haven't already.

One thing that can also amp all of this up is if we're adding prototypical gender scripts to any of this stuff. A whole lot of women have the idea that guys are the ones who are always supposed to get off -- and if they don't, their partner must have done something wrong or been somehow lacking -- while women may or may not. Scripts like that are so pervasive that few people are immune to them, especially in relationships in which there is one man and one woman. While people who either are not heterosexual and/or are not gendernormative can often be less impacted, I don't think that someone is automatically immune to these scripts by virtue of being outside those groups. In some ways, I get the impression some trans people can feel even more impacted by ideals like that because of the high pressure put on you to conform more and more strictly to hegemonic gender scripts than cis gender people in order to "prove" your gender is authentic. So, that's something else you two may want to check in on. This may be doubly loaded for her expressly because of her gender identity: both because she's trans and because she's a woman.

All the same, those gender scripts aren't often correct or accurate for people, including cis gender people. While there are some broad commonalities we can claim, for the most part no one group of people -- including the group that is all of us people -- gets off on any one thing, in any one setting, in any one kind of partnership or dynamic. Just like we all have good days, bad days and meh-days in other areas of our lives, the same goes with the sexual part of our lives. Our experiences are going to tend to vary a lot from day to day and life-phase to life-phase. It might be helpful to check in on that, too, and also to do some more talking about the ways each of you experiences pleasure, what pleases you, what makes you feel satisfied. That way, you can both be sure that if you're inclined to follow, intentionally or not, any scripts, the ones you're following are your own, authentic to each of you as individuals, rather than being more about general expectations or cultural sexual ideals. This may be one of those talks that winds up happening because of something not-so-pleasant that turns into a great takeaway that's beneficial for you both, one you might not have gotten to otherwise.

Let's talk some about her readiness now, and her feeling in hindsight that she may not have been as ready as she felt before having her actual experience.

I used to teach kickboxing. Now and then, someone would come into my class who was clearly a big-time beginner, so I'd suggest they take things slow and easy. But then they'd get really into it, feel full of energy, strong and gutsy, and want to push themselves further. So long as it didn't seem like they'd seriously injure themselves, I was not going to keep telling them to slow down because that would have been tremendously patronizing, and I needed to trust they knew themselves and their bodies better than I could. To treat them with respect, I needed to acknowledge that they were in a position to make their own choices about how much they wanted to push the envelope and let them decide how much, within reason. Sometimes those folks would do just fine and feel great during and after. Sometimes they'd feel great during, but come back next week and say their shoulders hurt like hell, and would say that this time, they were going to take it a little more easy. Sometimes they'd wind up running outside after a bunch of spinning kicks, toss their cookies on the sidewalk outside the gym and not even come back inside class at all that day, because they felt so embarrassed at having clearly done more than they were able to handle. There really was little I could do to forsee or control any of those outcomes beyond the basic warnings and gentle coaching I did already.

This is a lot like that. You're not psychic and neither is she. She did her best to be self-aware and to communicate where she was at with you, you did the same. You each gave each other the respect around that people give each other who are partners, not parents. You two clearly felt you wanted the same things at the same time, which you both chose to pursue. You both enjoyed the experience at the time, but you left it feeling like it was the right thing at the right time for you, and she left it feeling like it wasn't for her. That's okay. You're two different people, which means that often enough, you're not going to have the exact same experience with things you experience together.

We can all prepare ourselves for something we have not yet experienced all we want, and that preparation is important. At the same time, there are some things we are going to tend to only find out once we are actually doing or have done that thing. There's no shame in learning new or unexpected things about ourselves, no shame in making what we thought was a right call for us and finding out that maybe it wasn't, no shame in discovering that we were not actually ready for something we thought we were. This is how, after all, most of us learn a whole lot of things in our lives, by trial and error.

I'd let her know that she doesn't owe you any apologies: neither of you did anything wrong to each other here. I'd let her know that while however she's feeling is okay, that she doesn't need to feel ashamed or embarrassed about either her choice at the time or her feelings after-the-fact. It sounds like you've already let her know that you are 100% fine with how she's feeling, and 100% fine with where she wants to go from here. Now you can just let her know that whatever conclusions she comes to? It's also all good. You might also do some talking, after she's had some time, to try and unpack together why she felt she was feeling so bad: that might also help her better clarify what she needs to really feel ready.

It may help to let her know that the myth of the "perfect" first time with a partner is often just that. Sex, like life, is most frequently imperfect, and that's okay. First-time sex -- heck, sex any time at all -- with someone more often than not is not all floaty-awesome-flawless, but tends to carry complexities and uncomfortable vulnerabilities we may not forsee or anticipate, as you said. People are complicated, so expecting sex not to be, however common an expectation that is, doesn't make a lot of sense. Part of what can make sex so incredible is that it can sometimes allow us to be very real and flawed with each other, even when we're strongly vulnerable, so this experience being so real, and not the stuff of romance novels, is more good-thing than bad-thing in my book. Twenty years from now you're much more likely to remember things like all the communication you had around this than to remember one orgasm you had.

You asked about if I think it's be a good idea to step back from sex and give her some more time to sort through how she's feeling. That does sound like a good plan to me, so I'd put that out there to her, reminding her that as you have been in the past, you're just fine with waiting again. Perhaps obviously, if any of this felt triggering for her in terms of her past assault, if she's working with anyone in counseling, supporting her in talking to her counselor about this, and getting an extra opinion on if this is a sound pace for her, would also be a good move.

Lastly, I don't think you're being disrespectful because you found her pleasure and/or orgasm arousing and exciting. In the moment, that's what it was for both of you, and you can only really walk away with your own feelings, not with hers. You can hear, hold and understand hers, but you still had the experience you had, and it also sounds like the experience both of you had when you were having it was very positive. You can certainly talk this through with her if you both want to, but not only do I see nothing in how you're feeling that disrespects her, I see nothing in the way you describe your relationship that suggests you are likely to be disrespectful.

This is one of those questions where, when I read it, what I see are two people being so excellent to each other who are probably each feeling bad about things they just don't need to mostly because they so badly want to be excellent to each other.

There are limits to our interpersonal excellence. Even when we are interrelating magnificently, sometimes we or people we care for are still going to be disappointed, get their feelings hurt, or make missteps. There's never any avoiding that completely, because we're all only human and because we can get as close as possible to someone else, but we still can't live in their heads and hearts. As well, as we go through life, we're all in a neverending learning process to figure out what's right for us and how to go through life making choices well. None of us are born savant in that respect: we all tend to gradually improve at it over time.

The best we can do is to do our best at being honest with ourselves and honest with each other; at leaving room for each of us to be our own person; at communicating deeply, clearly and often, at setting and honoring boundaries and by being caring and loving, at making choices for ourselves that impact others with both of us in mind as much as possible. It appears you've both been doing all of those things beautifully. All of that will absolutely tend to limit how often you get or feel hurt or disappointed, and how deeply you do when it does happen. But it can't eradicate the risk of either.

If and when hurt or bummed-out-ness does still happen -- and it will -- then what we can do is use all of those great skills and intentions to be there for each other, to support one another, and to make allowances and adjustments as needed for others nd also for ourselves. In the end, that probably doesn't make anything perfect, but that's okay, because few things in life are ever perfect. (Also? I think perfection is overrated, and I say this to you as a terminal perfectionist, no less.)

It's clear you hate to see her feeling bad because you care about her, and you may also have some feelings of guilt of your own this. But sometimes, even when people do everything as right as they can, people are going to feel bad and will need to some time to work through that. I know that sucks and can make you feel precarious or insecure, and I also know it sucks do do everything as right as you can and have it not go as right as you want, especially with big deals. And yet, sometimes, that's just what happens. You and she both may need to work through some of your bad or guilty feelings alone before coming back at them together.

I think if you keep communicating, and keep supporting her as well as you obviously do, giving her what time she needs to process her feelings and figure out what her own next best steps are. If she decides she needs to put sex or certain kinds of sex on hold, I don't need to tell you the best response is to honor that: you already know that. If she comes back saying she still wants to pursue sex, I don't see any reason to distrust her in that, either, especially so long as you two continue to relate as well as you have been. You, also, get to take what time you need to process this and you, also, get to decide to step things back or make adjustments if you need to.

What I'll leave you with, besides my best wishes and a few extra links that I think may help, is just a reminder that you clearly have and have created the good stuff here, quite exceptionally. Having beautiful, marvelous relationships isn't about every aspect of them being flawless, but about accepting, supporting and caring for each other even when -- and maybe even especially when -- things don't go as we'd have liked or aren't exactly as we wanted. And from what I can gather, you two need very little help in that department. :)

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